(5S,8S,11S,12R)-allyl 11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-12-hydroxy-5-(2-(methylthio)ethyl)-3,6,9-trioxo-8-((tritylthio)methyl)-2-oxa-4,7,10-triazatetradecan-14-oate | 1351107-09-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5S,8S,11S,12R)-allyl 11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-12-hydroxy-5-(2-(methylthio)ethyl)-3,6,9-trioxo-8-((tritylthio)methyl)-2-oxa-4,7,10-triazatetradecan-14-oate
• CAS: 1351107-09-9
• 化学式: C₅₃H₅₉N₃O₇S₂
• 分子量: 914.199
• InChiKey: XUKSYHNBFLWRMU-BIZBAIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  65.0
• 可旋转键数：
  23.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  143.06
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (5S,8S,11S,12R)-allyl 11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-12-hydroxy-5-(2-(methylthio)ethyl)-3,6,9-trioxo-8-((tritylthio)methyl)-2-oxa-4,7,10-triazatetradecan-14-oate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.17h， 生成 (7R,11S,14S,17S,18R,E)-allyl 17-((S)-sec-butyl)-7,18-dihydroxy-11-(2-(methylthio)ethyl)-9,12,15-trioxo-1,1,1-triphenyl-14-((tritylthio)methyl)-2-thia-10,13,16-triazaicos-5-en-20-oate
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor

  摘要：

  Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM.

  DOI：

  10.1021/ol202197q
• 作为产物：
  描述：

  (4S,5S)-allyl 4-(tert-butoxycarbonylamino)-5-methyl-3-oxoheptanoate 在 钾硼氢 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.17h， 生成 (5S,8S,11S,12R)-allyl 11-((S)-sec-butyl)-1-(9H-fluoren-9-yl)-12-hydroxy-5-(2-(methylthio)ethyl)-3,6,9-trioxo-8-((tritylthio)methyl)-2-oxa-4,7,10-triazatetradecan-14-oate
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor

  摘要：

  Three diastereomers of burkholdac B were prepared by total synthesis, enabling the full stereochemical assignment of the natural product. It is proposed that burkholdac B is identical to thailandepsin A independently isolated by Cheng from the same strain of Burkholderia thailandensis. Burkholdac B is the most potent among depsipeptide histone deacetylase inhibitors in growth inhibition of the MCF7 breast cancer cell line with an IC50 of 60 pM.

  DOI：

  10.1021/ol202197q